111267-87-9Relevant academic research and scientific papers
Structure of a rearrangement product: 1-methyl-3-(5-amino-1-benzylimidazol-4-yl)-1,2,4-triazole, C13H14N6
Afshar, Carol,Berman, Helen M.,Sawzik, Patricia,Lessinger, Leslie,Lim, Benjamin B.,Hosmane, Ramachandra S.
, p. 533 - 544 (1987)
The title compound was prepared during the course of an attempt to synthesize 8-amino-3-benzyl-6-methylimidazotriazepine.The crystals are monoclinic, space group P21/c, a = 6.2375(5), b = 9.1070(8), c = 22.182(2) Angstroem, β = 91.797(7) deg, Z = 4.The structure was solved by direct methods and refined by least squares to R = 0.063 on all 2142 measured reflections.The imidazol-4-yl-triazole system is planar, conjugated, and aromatic.One hydrogen atom of the exocyclic amino group is involved in a bifurcated hydrogen bond, of which one branch is an intramolecular attraction to a triazole ring nitrogen atom, while the other ...
Rearrangements in Heterocyclic Synthesis: A Novel Translocation of an (N-Amino-N-methylamino)methylene Group from a Heterocyclic N-Amino-N-methylformamidine Side Chain to the Vinylogous Nitrile Function
Hosmane, Ramachandra S.,Lim, Benjamin B.,Burnett, Friedrich N.
, p. 382 - 386 (2007/10/02)
Reaction of the imidate 1-benzyl-4-cyano-5imidazole (5) with an equivalent of hydrazine provided 1-amino-9-benzyl-6-iminopurine (6), which, upon treatment which excess hydrazine, rearranged to 9-benzyl-6-hydrazinopurine (7).Reaction of 5 with methylhydrazine gave N-amino-N-methyl-N'-(1-benzyl-4-cyanoimidazol-5-yl)formamidine (8b).Thermolysis of 8b in refluxing toluene-methanol, catalyzed by trifluoroacetic acid, provided an equimolar mixture of 5-amino-1-benzyl-4-cyanoimidazole (9) and 3-(5-amino-1-benzylimidazol-4-yl)-1-methyl-1,2,4-triazole (10).Compound 9 was recycled to 8b via 5.The structure of 10 was established by spectral data coupled with an unequivocal synthesis.The conversion 8b to 10 represents a novel "translocative" rearrangement involoving the transfer of an NH2N(Me)CH= group from the imidazole 5-position to the nitrile function at position 4.Successful application of the rearrangement to the analogous pyrazole system is demonstrated.The rearrangement carries useful practical implications in the synthesis of the otherwise not easily accessible heterocycles of potential biological and medicinal significance.
CHEMISTRY OF THE 5:7-FUSED HETEROAROMATIC SYSTEMS: A NOVEL REARRANGEMENTINVOLVING THE IMIDAZOTRIAZEPINE AND PYRAZOLO-TRIAZEPINE SYSTEMS
Hosmane, Ramachandra S.,Lim, Benjamin B.
, p. 31 - 34 (2007/10/02)
A novel rearrangement which involves the potential intermediacy of an imidazo- or a pyrazolotriazepine is reported.
